Roma discrimination and stigmatization in Europe are well-documented, with urban scholars emphasizing pervasive prejudices and stereotypes alongside negative policy outcomes. However, the focus on Roma marginality has tended to centre on punitive state and urban governance to the neglect of everyday urban relations. In this article we focus on the micro manifestations of stigmatization—racialized urban encounters—and their neglected longer-term affects for Roma in Czechia and Romania. Ethnographic research and in-depth qualitative interviews with Roma respondents expose a complex, dynamic and multi-layered response to stigmatization that challenges the simplistic binary of resistance versus the internalization of stigma. The concept of fragmented habitus is deployed in capturing this dynamic process and providing a nuanced representation of the urban inhabitation of a long-term stigmatized and racialized position, beyond generic ‘Otherness’. We argue for more attention to the specificities and complexities of everyday relations and their affects in capturing the interdependence between urban encounters, the longer-term construction of Roma inferiority, and the heterogeneous, dynamic and ambivalent ways in which Roma inhabit their racialized urban position.